Real Estate Investment Properties for Sale in Chester, MD

Looking for investment property in Chester, MD with high ROI ?

Explore a variety of short-term homes & houses in Chester, MD. Invest wisely with VRBO & Chester, MD Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Condos for Sale in Chester, MD

Search for Condo for Sale in Chester, Maryland. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 15 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
54 QUEEN CAROLINE COURT CHESTER, MD Price Improvement...End Unit in Sought-After Queens Landing A Waterfront Lifestyle Awaits!...	2 beds \| 3 baths \| 1,280 sq.ft.	$415,000	Airbnb cash on cash: 7.85% Traditional cash on cash: 4.52% Airbnb Rental Income: $4662 Traditional Rental Income: $2400 Airbnb ROI: 7.85% Traditional ROI: 4.52%
34 QUEEN ANNE WAY CHESTER, MD Price Improvement on this CHESTER RIVER WATERFRONT Eastern Shore! Nestled within the water...	2 beds \| 3 baths \| 1,104 sq.ft.	$469,000	Airbnb cash on cash: 6% Traditional cash on cash: 4.56% Airbnb Rental Income: $4662 Traditional Rental Income: $3067 Airbnb ROI: 6% Traditional ROI: 4.56%
49 QUEEN GUINEVERE WAY CHESTER, MD Welcome to Queens Landing, where resort-style living meets the comfort of home. This beaut...	2 beds \| 3 baths \| 1,600 sq.ft.	$529,250	Airbnb cash on cash: 5.71% Traditional cash on cash: 4.44% Airbnb Rental Income: $4662 Traditional Rental Income: $3064 Airbnb ROI: 5.71% Traditional ROI: 4.44%
208 RINGNECK CT CHESTER, MD 208 Ringneck Court is a great home for the smart buyer! The 2 bedroom, 2 1/2 bathroom G...	2 beds \| 3 baths \| N/A	$339,900	Airbnb cash on cash: 9.08% Traditional cash on cash: 6.02% Airbnb Rental Income: $4662 Traditional Rental Income: $2721 Airbnb ROI: 9.08% Traditional ROI: 6.02%
170 HARRIER WAY #34 CHESTER, MD Open House this Sunday 8/24 from 12-2. New improved price of $795,000 and immediate occupa...	3 beds \| 3 baths \| N/A	$795,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 2.23% Airbnb Rental Income: $6279 Traditional Rental Income: $2981 Airbnb ROI: 5.02% Traditional ROI: 2.23%
170 HARRIER WAY #11 CHESTER, MD *Redfin powered by Rocket Mortgage Preferred Pricing* Enjoy with a 1% lower interest r...	2 beds \| 3 baths \| 2,003 sq.ft.	$499,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 4.02% Airbnb Rental Income: $4662 Traditional Rental Income: $3099 Airbnb ROI: 5.3% Traditional ROI: 4.02%
190 HARRIER WAY #11 CHESTER, MD Luxury 55+ Living at Four Seasons on Kent Island Move-In Ready & Priced to Sell! Welcome ...	2 beds \| 3 baths \| 2,003 sq.ft.	$540,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 2.17% Airbnb Rental Income: $4662 Traditional Rental Income: $2354 Airbnb ROI: 4.83% Traditional ROI: 2.17%
1000 HERONS NEST WAY #32 CHESTER, MD Move in this May and enjoy low-maintenance living in the sought-after 55+ community of Fou...	2 beds \| 2 baths \| N/A	$499,000	Airbnb cash on cash: 5.26% Traditional cash on cash: 2.75% Airbnb Rental Income: $4662 Traditional Rental Income: $2521 Airbnb ROI: 5.26% Traditional ROI: 2.75%
47 QUEEN ANNE WAY CHESTER, MD Enjoy resort style living every day in the gorgeous waterfront condo. 42' boat slip w/ wat...	2 beds \| 3 baths \| 1,440 sq.ft.	$598,000	Airbnb cash on cash: 4.93% Traditional cash on cash: 2% Airbnb Rental Income: $4662 Traditional Rental Income: $2059 Airbnb ROI: 4.93% Traditional ROI: 2%
15 QUEEN ANNE WAY #E CHESTER, MD The BIGGEST price drop yet!! Wake up to shimmering Chester River views and let every day f...	2 beds \| 3 baths \| 1,680 sq.ft.	$499,000	Airbnb cash on cash: 6.07% Traditional cash on cash: 4.57% Airbnb Rental Income: $4662 Traditional Rental Income: $2997 Airbnb ROI: 6.07% Traditional ROI: 4.57%
170 HARRIER WAY #33 CHESTER, MD This Chester model has scenic views of the river, beautiful sunrises, and an incredible di...	2 beds \| 3 baths \| 1,900 sq.ft.	$499,950	Airbnb cash on cash: 5.25% Traditional cash on cash: 3.45% Airbnb Rental Income: $4662 Traditional Rental Income: $2853 Airbnb ROI: 5.25% Traditional ROI: 3.45%
1000 HERONS NEST WAY #22 CHESTER, MD Welcome to 1000 Heron's Nest Way. This Chester model has scenic, seasonal views of Macum C...	2 beds \| 3 baths \| 1,900 sq.ft.	$488,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 4.47% Airbnb Rental Income: $4662 Traditional Rental Income: $3249 Airbnb ROI: 5.44% Traditional ROI: 4.47%
35-F QUEEN ANNE WAY CHESTER, MD Welcome to 35F Queen Anne Way in Queens Landing! This lakefront updated home offers 2 bedr...	2 beds \| 3 baths \| N/A	$354,900	Airbnb cash on cash: 9.1% Traditional cash on cash: 6% Airbnb Rental Income: $4662 Traditional Rental Income: $2662 Airbnb ROI: 9.1% Traditional ROI: 6%
108 BODYS NECK ROAD CHESTER, MD Coming Soon in Bayside on Kent Island Resort-Style Island Living with Unmatched Water View...	3 beds \| 3 baths \| 1,791 sq.ft.	$499,900	Airbnb cash on cash: 8.88% Traditional cash on cash: 4.8% Airbnb Rental Income: $6279 Traditional Rental Income: $3136 Airbnb ROI: 8.88% Traditional ROI: 4.8%
807 AUCKLAND WAY CHESTER, MD PRICE REDUCED! Waterside Living on Kent Island! Discover the perfect blend of comfort an...	3 beds \| 4 baths \| 2,100 sq.ft.	$482,090	Airbnb cash on cash: 9.24% Traditional cash on cash: 5.78% Airbnb Rental Income: $6279 Traditional Rental Income: $3486 Airbnb ROI: 9.24% Traditional ROI: 5.78%

Your search for investment property begins and ends here

Condos for Sale in Chester, MD

54 QUEEN CAROLINE COURT

CHESTER, MD

2 beds | 3 baths | 1,280 sq.ft.

$415,000

Airbnb cash on cash: 7.85%

Traditional cash on cash: 4.52%

Airbnb Rental Income: $4662

Traditional Rental Income: $2400

Airbnb ROI: 7.85%

Traditional ROI: 4.52%

34 QUEEN ANNE WAY

CHESTER, MD

2 beds | 3 baths | 1,104 sq.ft.

$469,000

Airbnb cash on cash: 6%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $4662

Traditional Rental Income: $3067

Airbnb ROI: 6%

Traditional ROI: 4.56%

49 QUEEN GUINEVERE WAY

CHESTER, MD

2 beds | 3 baths | 1,600 sq.ft.

$529,250

Airbnb cash on cash: 5.71%

Traditional cash on cash: 4.44%

Airbnb Rental Income: $4662

Traditional Rental Income: $3064

Airbnb ROI: 5.71%

Traditional ROI: 4.44%

208 RINGNECK CT

CHESTER, MD

2 beds | 3 baths | N/A

$339,900

Airbnb cash on cash: 9.08%

Traditional cash on cash: 6.02%

Airbnb Rental Income: $4662

Traditional Rental Income: $2721

Airbnb ROI: 9.08%

Traditional ROI: 6.02%

170 HARRIER WAY #34

CHESTER, MD

3 beds | 3 baths | N/A

$795,000

Airbnb cash on cash: 5.02%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $6279

Traditional Rental Income: $2981

Airbnb ROI: 5.02%

Traditional ROI: 2.23%

170 HARRIER WAY #11

CHESTER, MD

2 beds | 3 baths | 2,003 sq.ft.

$499,000

Airbnb cash on cash: 5.3%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $4662

Traditional Rental Income: $3099

Airbnb ROI: 5.3%

Traditional ROI: 4.02%

190 HARRIER WAY #11

CHESTER, MD

2 beds | 3 baths | 2,003 sq.ft.

$540,000

Airbnb cash on cash: 4.83%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $4662

Traditional Rental Income: $2354

Airbnb ROI: 4.83%

Traditional ROI: 2.17%

1000 HERONS NEST WAY #32

CHESTER, MD

2 beds | 2 baths | N/A

$499,000

Airbnb cash on cash: 5.26%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $4662

Traditional Rental Income: $2521

Airbnb ROI: 5.26%